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Chapter 19: Q70 (page 763)

Although p-hydroxybenzoic acid is less acidic than benzoic acid, o-hydroxybenzoic acid is slightly more acidic than benzoic acid. Explain this result.

Short Answer

Expert verified

This occurs due to the stabilization of carbanion.

Step by step solution

01

p-hydroxybenzoic acid

The p-hydroxybenzoic acid is less acidic than benzoic acid. It has an alcohol group at para position to the acidic group of the benzoic acid. Theresonance effect destabilizes the conjugate base.

02

Step 2: o-hydroxybenzoic acid

The o-hydroxybenzoic acid is more acidic than benzoic acid.It has an alcohol group at ortho position to the acidic group of the benzoic acid.

03

Explanation

The p-hydroxybenzoic acid hasan OH group, whichdonates electron density by its resonance effect, destabilizing the conjugate base and making the acid less acidic than benzoic acid.

Destabilized conjugate base

The o-hydroxybenzoic acid has intramolecular hydrogen bonding, stabilizing the conjugate base and making the compound more acidic than benzoic acid.

Stabilized conjugate base

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Most popular questions from this chapter

Threonine is a naturally occurring amino acid that has two stereogenic centers.

a. Draw the four possible stereoisomers using wedges and dashes.

b. The naturally occurring amino acid has the 2S,3R configuration at its two stereogenic centers. Which structure does this correspond to?

Question: Give the IUPAC name for each compound.

a.

b.

c.

d.

e.

f.

Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base.

(a) Explain why the ${pK}_{a}$ for loss of the first proton ( ${pK}_{a 1}$ ) is lower for phthalic acid than isophthalic acid.

(b) Explain why the ${pK}_{a}$ for loss of the second proton ( ${pK}_{a 2}$ ) is higher for phthalic acid than isophthalic acid.

As we will see in Chapter 23, C-H bonds are sometimes more acidic than O-H bonds. Explain why the ${pK}_{a}$ of ${CH}_{2} {(CHO)}_{2}$ is lower than the ${pK}_{a}$ of $OH {({CH}_{2})}_{3} OH$ (9 vs. 16).

Can octane and octan-1-ol be separated using an aqueous extraction procedure? Explain why or why not.

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